The reduction of 3-oxatricyclo[3.2.1.0 2,4 ]octane-endo-6-carbonitrile by lithium aluminum hydride is completed by the formation of exo-2-hydroxy-4-azatricyclo[4.2.1.0 3,7 ]nonane with the structure confirmed (1) by the analysis of 1 H, 13 C, 14 N, and 17 clo[4.2.1.0 3,7 ]nonane prepared by an alternative synthesis, viz., epoxidation of N-(p-bromophenylsulfonyl)bicyclo[2.2.1]hept-2-en-endo-5-methylamine. The reduction of 3-oxatricyclo [3.2.1.0 2,4 ]octane-exo-6-carbonitrile affords the epoxide, 3-oxatricyclo[3.2.1.0 2,4 ]octane-exo-6-methylamine. Different behaviors of stereoisomers are discussed; analysis of the *To whom correspondence should be addressed. coefficients of the atomic orbitals in the MO LCAO equation (AM1 method) has been made, and the strengths of the C-O bonds in the epoxy ring has been analyzed.
O NMR spectra and the two-dimensional spectra (COSY-experiment); (2) by comparison with 1 H and 13 C NMR spectra of the corresponding oxygen analog of heterobrendane; (3) by the calculation of the vicinal constants for the spinspin interaction in the molecules of both analogs by the MMX program; and (4) by transformation into N-(p-bromophenylsulfonyl)-exo-2-hydroxy-4-azatricy-